Photo-and thermoresponsive N-salicylideneaniline derivatives: solid-state studies and structural aspects

Hulushe, Siyabonga T; Malan, Frederick P; Hosten, Eric C; Lobb, Kevin A; Khanye, Setshaba D; Watkins, Gareth M

Title: Photo-and thermoresponsive N-salicylideneaniline derivatives: solid-state studies and structural aspects
Creator: Hulushe, Siyabonga T
Creator: Malan, Frederick P
Creator: Hosten, Eric C
Creator: Lobb, Kevin A
Creator: Khanye, Setshaba D
Creator: Watkins, Gareth M
Subject: To be catalogued
Date Issued: 2022
Date: 2022
Type: text
Type: article
Identifier: http://hdl.handle.net/10962/451137
Identifier: vital:75021
Identifier: xlink:href="https://pubs.rsc.org/en/content/articlehtml/2022/nj/d1nj03056f"
Description: N-Salicylideneaniline (SA) and its derivatives are known to possess chromism upon exposure to external stimuli. Herein, we present mechanochemical synthesis of a series of photo-and thermoresponsive SAderivatives and report on solid-state stabilisation of their tautomeric forms either by change in temperature or by photoirradiation. The influence of UV light on proton transfer between the enol-imine (EI) and keto-amine (KA) forms was investigated at l1 = 254 and l2 = 365 nm. Differential scanning calorimetry (DSC) measurements provided extra information on the thermodynamic relationship between the prototropic tautomers, and their exposition to liquid nitrogen, combined with variable temperature single-crystal X-ray diffraction (VT-SCXRD) and spectroscopic data, ascertained structural reasons for the intrinsic thermo-optical properties of the compounds. A series of structural determinations between 150 and 300 K further shed light on the thermomechanical behaviour exhibited by the thermoresponsive compounds. By virtue of calorimetry we were able to demonstrate proton transfer via the intramolecular ON hydrogen bond over the temperature range 193–453 K. This present work demonstrates the importance of applying complementary analytical techniques and appropriate approaches for understanding the switching behaviour between the EI and KA forms. Furthermore, the assertion that it is predominantly the planarity (j o 251) that determines thermochromaticity is questioned.
Format: computer
Format: online resource
Format: application/pdf
Format: 1 online resource (11 pages)
Format: pdf
Publisher: Royal Society of Chemistry
Language: English
Relation: New Journal of Chemistry
Relation: Hulushe, S.T., Malan, F.P., Hosten, E.C., Lobb, K.A., Khanye, S.D. and Watkins, G.M., 2022. Photo-and thermoresponsive N-salicylideneaniline derivatives: solid-state studies and structural aspects. New Journal of Chemistry, 46(43), pp.20940-20950
Relation: New Journal of Chemistry volume 46 number 43 p. 20940 2022 1369-9261
Rights: Publisher
Rights: Use of this resource is governed by the terms and conditions of the Royal Society of Chemistry Terms and Conditions Statement (https://0-www.rsc.org.wam.seals.ac.za/help-legal/)
Rights: Open Access

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